Chicago Seminars Go Online For 2020

Filed Under: Advice, Misc.

One of the longest standing annual miles & points “events” is the Chicago Seminars, which has been held at the Holiday Inn in Elk Grove, Illinois (nearish to the Chicago O’Hare Airport) for the past ten years.

Ten years. I’m getting old.

Ben and I actually met in-person for the first time at a Chicago Seminars many moons ago, so the event is always covered in nostalgia for me. The fact that Howie Rappaport has this event down to a science so that very little changes year to year probably helps with that. While there are plenty of new folks each year, seeing the same faces in the same format (including the staff at the host hotel) always makes it feel more like a family reunion to me than anything else.

And so while we’ve all become somewhat desensitized about in-person events being canceled in 2020, I was still a little sad at the thought of this gathering not happening.

So I’m happy to share that the Chicago Seminars will be returning(ish) for an 11th year, and will be held as an online “Variety Show” on Saturday, October 17th.

Stefan Krasowski of Rapid Travel Chai and Every Passport Stamp has taken up the organization and production mantles, and describes the vision for the virtual meet-up as follows:

This will not be a virtual “conference”. Rather it will be a telethon with one surprise guest after another. Very live, very chaotic, people popping in and out, with a mix of Q&A with me and other guests, a few slots with speakers sharing rapid-fire on a topic, and a generally high-energy event.

The livestream event will include an assortment of speakers, including myself, along with:

  • Dia Adams
  • Matthew Klint
  • Howie Rappaport & Rick Ingersoll
  • Nick Reyes & Stephen Pepper
  • Jamal Robinson
  • Shawn Coomer & Mark Ostermann
  • Dave Homyak
  • Thomas Carnevale
  • Zachary Finkelstein
  • Henning Mente
  • Marty Paz & JJ Todd
  • An assortment of “celebrity” cameos 😉

There will be virtual happy hours on Friday as well, in hopes of trying to replicate that experience of hanging out in the hallways and otherwise meeting new folks from the community — you’ll get information on that when you register.

There will be a public “kick-off” Thursday, October 15 at 7-8 pm Eastern, — “A Decade of Chicago Seminars” livestream with event founders Rick Ingersoll and Howie Rappaport, hosted by Stefan Krasowski. The YouTube livestream is available free of charge to all.

As usual, this is an all-volunteer event, with all the proceeds going to charity. Tickets this year are just $11 (given the general lack of expenses with a virtual gathering). You can find the Chicago Seminars ticket registration link here.

As is traditional for this event, there is a very diverse assortment of speakers spread over two dozen sessions. That will be replicated here, with a mix of topics and speakers, along with some surprise “celebrity” cameos 😉

This is typically a very low-key and enjoyable event, which generally attracts a good mix of people new to miles and points and savvy veterans. Hopefully that can be replicated a bit with this virtual format!

  1. I’m really glad the Chicago Seminars will be continuing this year. I always get lots of new ideas, strategies and techniques there, too many even to implement them all.

    Hooray for virtual this year, hoping for physical next year!

  2. This event is also super nostalgic for me. Although I obviously don’t have the same intimate connection with the staff and presenters as the true heavy hitters, I did chat with you and Ben for the first time in 2014 when I was still fairly new to this whole thing and that has stayed with me.

    Absolutely loved the laid-back approach and being able to mingle with like-minded people in an informal setting. The neat prizes you guys brought were always awesome

    Can’t recommend it enough to people who are on the fence.

  3. I second @Simon’s comment above. I have two young kids, so I can attend on a Saturday. I will happily pay $11 to be able to access the recording at a later time. Do you guys know if it’s going to be recorded?

Leave a Reply

If you'd like to participate in the discussion, please adhere to our commenting guidelines. Your email address will not be published. Required fields are marked *